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Note that this is dangerous, since gethttpsforfree.com can save your private key and therefore is able to decrypt all content.
That's not correct - the site asks for a CSR, which doesn't include your private key. The private key (and ACME account key) doesn't leave your device.
Just chiming in, gethttpsforfree.com does not ever get your private key. Only a certificate signing request that is generated using your private key. There is no such private key risk involved using this site.
It seems like a good idea. I think some of the friction is related to the historic decline in the quality and trustworthyness of the free Windows software. In a world where even Java comes with crapware, .exe is a problematic format for many [despite being easy to deploy and get running].

My gut is that the wind is behind open source as the successor to free-ware and shareware in the Windows world. It's certainly becoming the favored alternative when paid developer tools aren't selected.

Good luck.

Almost all of the tools I use professionally on Windows are open source.

VS Code, Cygwin, Git, Go, PuTTY, Vagrant, VirtualBox covers 99% of my workflow on Windows.

ooc, most if not all of these software are second-class citizens on windows, and would perform much better under linux/bsd (as in OSX). how come you are running windows?
I mostly run Linux, but I maintain a Windows machine for the purposes of games / music production etc.

Most of my work is done in Linux, but my laptop runs Windows (hence my use of the phrase "Windows workflow").

I'm completely competent in OSX, and have regularly used it since it's release, but I don't really like it, and don't own a Mac (this choice is purely personal, and I don't hate Mac owners).

Hope that makes sense! Sorry for the ambiguity :-)

EDIT: With both KSP and Snow (pretty much the only games I play) having Linux builds, it's really Ableton that keeps me away from a pure Linux experience. Ableton 9 doesn't really run that well under Wine!

We use this:

https://github.com/Lone-Coder/letsencrypt-win-simple

Works like an absolute charm.

Ah good mention, didn't know about this tool. Looks very sleek!

I wanted to avoid building a solution to do the whole communication as I was pretty happy with the website functionality. This tool is mostly to enable you to use the website on windows and to automate a lot of the annoying Windows stuff while still retaining the option to use the website or the Let's Encrypt client in a pinch :)